Hydrosilanes are not always reducing agents for carbonyl compounds, II: Ruthenium-catalyzed deprotection of tert-butyl groups in carbamates, carbonates, esters, and ethers

European Journal of Organic Chemistry

Volumn , Issue 6, 2010, Pages 1021-1025

  Hanada, Shiori ^a   Yuasa, Akihiro ^a   Kuroiwa, Hirotaka ^a   Motoyama, Yukihiro ^a   Nagashima, Hideo ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Cleavage reactions; Hydrosilanes; Protecting groups; Ruthenium; Si H activation

Indexed keywords

EID: 76449094707     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901279     Document Type: Article

References (30)

1. a) I. Ojima in The Chemistry of Organic Silicon Compounds (Ed.: S. Patai, Z. Rappoport), Wiley, New York, 1989, part 2, ch. 25, pp. 1479-1526;
2. b) B. Marciniec, Comprehensive Handbook on Hydrosilylation, Pergamon Press, Oxford, 1992;
3. c) B. Marciniec in Applied Homogeneous Catalysis with Organometallic Compounds (Ed.: B. Cornils, W. A. Herrmann), WileyVCH, Weinheim, 1996, vol.1, ch. 2;
4. d) H. Vorbrüggen in Silicon-Mediated Transformations of Functional Groups, WileyVCH, Weinheim, 2004;
5. e) B. Marciniec (Ed.), Hydrosilylation: A Comprehensive Review on Recent Advances (Advances in Silicon Science), Springer, Berlin, 2008;
6. f) R.G. Andersson, I. J. Munslow (Eds.), Modern Reduction Methods, Wiley-VCH, Weinheim, 2008, ch. 4 and 8.
7. Representative papers: a) R. Kuwano, M. Takahashi, Y Ito, Tetrahedron Lett. 1998, 39, 1017-1020;
8. b) K. Selvakumar, K. Rangareddy, J. F. Harrod, Can. J. Chem. 2004, 82, 1244-1248;
9. c) T. Ohta, M. Kamiya, M. Nobumoto, K. Kusui, I. Furukawa, Bull. Chem. Soc. Jpn. 2005, 78, 1856-1861;
10. d) A. C. Fernandes, C. C. Romão, J. Mol. Catal. A 2007, 272, 60-63.
11. a) H. Nagashima, A. Suzuki, T. Iura, K. Ryu, K. Matsubara, Organometallics 2000, 19, 3579-3590;
12. b) K. Matsubara, T. Iura, T. Maki, H. Nagashima, J. Org. Chem. 2002, 67, 4985-4988;
13. c) Y Motoyama, C. Itonaga, T. Ishida, M. Takasaki, H. Nagashima, Org. Synth. 2005, 82, 188-195;
14. d) Y Motoyama, K. Mitsui, T. Ishida, H. Nagashima, J. Am. Chem. Soc. 2005, 127, 13150-13151;
15. e) S. Hanada, T. Ishida, Y. Motoyama, H. Nagashima, J. Org. Chem. 2007, 72, 7551-7559;
16. f) H. Sasakuma, Y. Motoyama, H. Nagashima, Chem. Commun. 2007, 4916-4918.
17. S. Hanada, Y. Motoyama, H. Nagashima, Eur. J. Org. Chem. 2008, 4097-4100.
18. Fe-catalyzed reactions: a) S. Zhou, D. Addis, S. Das, K. Junge, M. Beller, Chem. Commun. 2009, 4883-4885;
19. b) S. Zhou, K. Junge, D. Addis, S. Das, M. Beller, Org. Lett. 2009, 11, 24612464.
20. [3a,3e]
21. P. G. M. Wuts, T. W. Greene in Greene's Protective Groups in Organic Synthesis, 4th. ed., Wiley, New York, 2007, ch. 2, 3, 5, and 7.
22. a) J. R. Hwu, M. L. Jain, S.-C. Tsay, G. H. Hakimelahi, Tetrahedron Lett. 1996, 37, 2035-2038;
23. b) J. S. Yadav, B. V. S. Reddy, K. S. Reddy, K. B. Reddy, Tetrahedron Lett. 2002, 43, 1549-1551.
24. G. A. Olah, S. C. Narang, Tetrahedron 1982, 38, 2225-2277.
25. H. Nagashima, C. Itonaga, J. Yasuhara, Y. Motoyama, K. Matsubara, Organometallics 2004, 23, 5779-5786.
26. a) S. Hanada, Y. Motoyama, H. Nagashima, Tetrahedron Lett. 2006, 47, 6173-6177;
27. b) S. Hanada, E. Tsutsumi, Y. Motoyama, H. Nagashima, J. Am. Chem. Soc. 2009, 131, 15032-15040;
28. c) Y. Motoyama, M. Aoki, N. Takaoka, H. Nagashima, Chem. Commun. 2009, 1574-1576;
29. d) Y Sunada, H. Kawakami, T. Imaoka, Y. Motoyama, H. Nagashima, Angew. Chem. Int. Ed. 2009, 48, 9511-9514.
30. P. Pawluc, B. Marciniec, I. Kownacki, H. Maciejewski, Appl. Organomet, Chem. 2005, 19, 49-54.